Asymmetric Reduction of Quinolines: A Competition between Enantioselective Transfer Hydrogenation and Racemic Borane Catalysis

被引：9
作者：
Gao, Bochao [1 ,2 ]
Han, Zaiqi [1 ,2 ]
Meng, Wei [1 ,2 ]
Feng, Xiangqing [1 ,2 ]
Du, Haifeng [1 ,2 ]
机构：
[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 05期
基金：
中国国家自然科学基金;
关键词：
ORGANOCATALYTIC TRANSFER HYDROGENATION; METAL-FREE HYDROGENATIONS; CHIRAL PHOSPHORIC-ACID; FRUSTRATED LEWIS PAIRS; BRONSTED ACID; BIOMIMETIC REDUCTION; HANTZSCH ESTERS; NAD(P)H MODEL; IMINES; LIGANDS;
D O I：
10.1021/acs.joc.2c02905
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A chiral phosphoric acid catalyzed asymmetric transfer hydro-genation of quinolines with regenerable dihydrophenanthridine derived by a borane-catalyzed hydrogenation of phenanthridine under H2 has been successfully realized. Despite the competition of a racemic hydrogenation pathway, a variety of tetrahydroquinolines were furnished in high yields with up to 91% ee.
引用
收藏
页码：3335 / 3339
页数：5
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